Chlorotrimethylsilane → N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-beta-D-erythro-pentofuranosyl]guanine

HRID 2361725Notes

Reaction equation

HRID 2361725 reaction equation
[C:1]([C@@:3]1([F:21])[C@H:7]([OH:8])[C@@H:6]([CH2:9][OH:10])[O:5][C@H:4]1[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][CH:14]=[N:15][C:16]=2N)#[CH:2].C[Si](Cl)(C)C.CO[C:29]1[CH:48]=[CH:47][CH:46]=[CH:45][C:30]=1[C:31](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[NH4+:49].[OH-:50].C([O:54][CH2:55]C)(=O)C>N1C=CC=CC=1>[CH3:55][O:54][N:49]([C:31]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:30]1[CH:29]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:14]1[NH:15][C:16](=[O:50])[C:17]2[N:18]=[CH:19][N:11]([C@@H:4]3[O:5][C@H:6]([CH2:9][OH:10])[C@@H:7]([OH:8])[C@@:3]3([C:1]#[CH:2])[F:21])[C:12]=2[N:13]=1

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 14429619Methoxytrityl chlorideHCID 866247809-[(2R)2-Deoxy-2-C-ethynyl-2-fluoro-beta-D-erythro-pentofuranosyl]adenine

Product 1

HCID 136343925N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-beta-D-erythro-pentofuranosyl]guanine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 7i (5.18 mmol) in pyridine (7 ml/mmol) was added trimethylsilyl chloride at room temperature. The mixture was stirred at room temperature for 6 hours. Methoxytrityl chloride (6.21 mmol) was then added and the reaction mixture was stirred at room temperature for 16 hours and 2 hours with NH4OH (4 ml/mmol). The mixture was diluted with ethyl acetate, washed with H2O, sat NaHCO3 solution and sat NaCl solution, dried over Na2SO4, filtered and evaporated. The crude material was purified by silica gel chromatography (DCM/MeOH) to yield the title compound. Yellowish oil. Molecular Formula C32H28FN5O5.

Workup

  1. washwashed with H2O
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-882d5776bf6f476f956ae2a3d5e77893
Source dataset
uspto-grants-2014_04
Patent number
US08691788B2

Reaction notes

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